I think a lot of voters are more concerned about perception than facts, and we all know that facts can be interpreted in many different ways, so I don't hold a lot of value in fact checkers.
Often, when I do take the time to read some of the fact checking they write all this stuff about the facts and then slap a rating on the statement or statements (or past actions), but when you read the stuff prior to the rating you see that they made an interpretation based on their world view to come to that rating. A lot of this stuff stuff is subjective but requires an objective view. The fact checking phenomenon fails at this, which makes them untrustworthy.
I was more interested in seeing the tweets and interviews that contradicted Trump's claims that he "never said that." I suspect he says a lot of things without really thinking about the long-term implications.
I think Trump is a person who is often misinterpreted if you are not from or not familiar with how people from the Northeastern region speak and I can see how that could pose an issue. He's definitely a New Yorker and more generally a New Englander, and not everyone in the United States is familiar with how they communicate / convey their thoughts to others in that region.
He says stuff, yes, but I can see how some groups of people (or people from certain regions of the United States) don't get it when he's joking or intentionally exaggerating for emphasis or to make a point. If Trump is guilty of anything, its assuming that all the people in the United States, regardless of which part they are from or have lived in, understand the cultural, linguistic and personality (with respect to communication) differences from New England to other parts of the country.
Applying Occam's razor, I just think he's opportunistic and intellectually challenged.
Everybody is entitled to their opinion. :)